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Street View
$2,295,000
Monthly Est:$11,423
31 Beds
- 29 Baths
14 full baths + 15 half baths
38,415sqft
349 Old Stockbridge Rd, Lenox, MA 01240
$2,295,000
$11,423/moEst:
Get Pre-Approved
Single Family Residence
Built in 1903
$-- HOA
11.9 acres lot
$60/sq.ft
Description
A singular opportunity to reimagine one of Lenox's historic Berkshire estates. Set on 11.90± acres just minutes from downtown Lenox and the cultural attractions of the Berkshires, Overlee was built in 1903 for Samuel Frothingham and designed by Adams & Warren in an Elizabethan/Jacobean Revival style.The original mansion remains at the heart of the property, surrounded by broad lawns and buildings added during its later evolution into an educational campus. Much of the character of the original country house remains, including handsome woodwork, substantial fireplaces, gracious rooms, and a beautiful ballroom. Most recently used for classrooms and administrative functions, the mansion was originally designed as a residence, with bedrooms on its upper floors.Beyond the main house are two dormitory residences with approximately 24 bedrooms and shared common spaces, a separate multi-level building with commercial kitchen and dining facilities, classrooms, offices, library, conference and infirmary spaces, a substantial gymnasium, and additional support buildings. For a residential buyer, this unusual collection offers possibilities for guest and staff accommodations, studios, offices, recreation, wellness, or a multi-generational Berkshire estate, subject to applicable approvals.The gymnasium could accommodate fitness, indoor tennis, pickleball, squash, or other private amenities. Existing infrastructure includes public water, multiple electrical services, mixed heating systems, central air in the dormitories and gymnasium, commercial sprinklering in select buildings, extensive parking, and established internal circulation.Hillcrest currently operates on the campus under a lease through June 2027 and presently anticipates vacating in February/March 2027.This offering is for 349 Old Stockbridge Road only. The property is also marketed as part of a combined offering with 40 Frothingham Crossing; see MLS #73518284.For its next steward, Overlee offers the rare chance to inherit not simply a house, but an entire Berkshire estate—historic architecture, expansive grounds, and a collection of buildings ready to support a new vision.Offered at $2,295,000.
- Houzeo last checked: 54 minutes ago
- Listing updated: September 8, 2026 at 6:37 pm
- Listing Provided by: Selina Lamb (413) 329-0435 | Birch Properties (413) 613-4363
- Source: MLS Property Information Network-MA | MLS#: 73567764

Property Details
Status
Active
Type
Single Family Residence
No. of Stories
-
County
City
Neighborhood
--
Year Built
1903
HOA Fees
-
Finished Area
38,415 sqft
Lot Size
11.9 acres lot
Basement Area
- sqft
MLS Name
MLS Property Information Network
MLS Number
73567764
MLS Status
Active
Days on Market
61

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Location
Facts & Features
Rooms
Bedrooms & bathrooms
Bedrooms: 31
Bathrooms: 29
Interior
Exterior Features
Patio, Pool Inground, Storage, Sprinkler System
Sewer
Private Sewer
Appliances
Electric Water Heater, Dishwasher, Microwave, Indoor Grill, Refrigerator, Freezer, Washer, Dryer, Range Hood
Heating
Central, Forced Air, Oil
Flooring
Wood, Tile, Carpet, Laminate
Cooling
Central Air, Wall Unit(s), Ductless
Construction
Year Built
Year Built: 1903
Home type
Single Family Residence
Construction Materials
Frame, Brick
Foundation Details
Stone
Architectural Style
Victorian, Mid Century Modern
Roof
Metal, Asphalt/composition Shingles
Utilities & Energy
Pool Features
In Ground
Water Source
Public
Basement
Walk Out Access, Interior Entry, Concrete
Electric
100 Amp Service, 200+ Amp Service
Parking Features
Detached, Paved Drive, Off Street, Paved, Unpaved
Other Features
Disclosures
This Listing Does Not Include Property At 40 Frothingham Crossing, Lenox.
Patio And Porch Features
Patio
Lot Features
Underground Storage Tank
Price History
| Date | Event | Price |
|---|---|---|
08/25/2026 Source: | Price Increased | $3,195,000 +39.22% $0/sqft |
08/25/2026 Source: | Price Decreased | $2,295,000 -38.80% $0/sqft |
07/20/2026 Source: | Listed for Sale | $3,750,000 $0/sqft |
06/16/2026 Source: | Pending | $3,750,000 $0/sqft |
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